ChemicalBook > Product Catalog > Organic Chemistry > Hydrocarbons and derivatives > Hydrocarbon halides > 1,2-Dichloropropane
1,2-Dichloropropane Chemical Properties
- Melting point:−100 °C(lit.)
- Boiling point:95-96 °C(lit.)
- Density 1.156 g/mL at 25 °C(lit.)
- vapor density 3.89 (vs air)
- vapor pressure 40 mm Hg ( 19.4 °C)
- refractive index n
- Flash point:40 °F
- storage temp. Refrigerator
- solubility Miscible with organic solvents (U.S. EPA, 1985).
- form Liquid
- color Clear colorless to light yellow
- explosive limit14.5%
- Water Solubility 3 g/L (20 ºC)
- Merck 14,7854
- BRN 1718880
- Henry's Law Constant0.81, 1.06, 1.32, 2.01, and 2.74 at 2.0, 6.0, 10.0, 18.0, and 25.0 °C, respectively (EPICS-SPME, Dewulf et al., 1999)
- Exposure limitsPotential occupational carcinogen. NIOSH REL: IDLH 400 ppm; OSHA PEL: TWA 75 ppm (350 mg/m3); ACGIH TLV: TWA 75 ppm, STEL 110 ppm (adopted).
- Stability:Stale. Highly flammable. Incompatible with strong oxidizing agents.
- CAS DataBase Reference78-87-5(CAS DataBase Reference)
- NIST Chemistry ReferencePropane, 1,2-dichloro-(78-87-5)
- IARC1 (Vol. 41, Sup 7, 71, 110) 2017
- EPA Substance Registry System1,2-Dichloropropane (78-87-5)
- Hazard Codes F,Xn,T
- Risk Statements 11-20/22-39/23/24/25-23/24/25-23/25
- Safety Statements 16-24-45-36/37-7
- RIDADR UN 1279 3/PG 2
- WGK Germany 3
- RTECS TX9625000
- Autoignition Temperature1035 °F
- TSCA Yes
- HazardClass 3
- PackingGroup II
- HS Code 29031990
- Hazardous Substances Data78-87-5(Hazardous Substances Data)
- ToxicityLD50 orally in rats: 1.19 ml/kg (Smyth)
1,2-Dichloropropane Usage And Synthesis
- Chemical Propertiescolourless liquid
- Chemical PropertiesDichloropropane is a colorless stable liquid. Sweet, chloroform-like odor. The odor threshold in air is 0.25 ppm.
- Physical propertiesClear, colorless liquid with a sweet, chloroform-like odor. The average least detectable odor threshold concentration in water at 60 °C was 0.10 mg/L (Alexander et al., 1982). Experimentally determined detection and recognition odor threshold concentrations were 1.2 mg/m3 (260 ppbv) and 2.4 mg/m3 (520 ppbv), respectively (Hellman and Small, 1974).
- Uses1,2-Dichloropropane is used as a soil fumigant, often as a mixture with 1,3-dichloropropene to control nematodes and soil pests.
- Uses1,2-Dichloropropane is a byproduct in the production of epichlorohydrin (E582310), an important industrial chemical, is a bifunctional alkylating agent with the potential to form DNA cross-links.
- UsesSolvent for oils, fats, resins, waxes, rubber; in ion exchange manufacture; in photographic film production; paper coating; petroleum catalyst regeneration. Has been used as a soil fumigant.
- UsesSoil fumigant for nematodes.
- General DescriptionColorless watery liquid with a sweet odor. Sinks in water. Produces an irritating vapor.
- Air & Water ReactionsHighly flammable. Insoluble in water.
- Reactivity Profile1,2-Dichloropropane reacts with strong oxidizers and strong acids. 1,2-Dichloropropane also reacts with aluminum. When confined, this reaction can lead to an explosion. 1,2-Dichloropropane is incompatible with bases and aluminum alloys. 1,2-Dichloropropane will attack some forms of plastics, rubber and coatings.
- HazardFlammable, dangerous fire risk, explosive limits in air 3.4–14.5%. Toxic by ingestion and inhalation. Upper respiratory tract irritant and body weight effects. Questionable carcinogen.
- Health HazardContact with skin or eyes may cause irriation.
- Fire HazardSpecial Hazards of Combustion Products: Toxic and irritating gases may be generated.
- Chemical ReactivityReactivity with Water No reaction; Reactivity with Common Materials: No reaction; Stability During Transport: Stable; Neutralizing Agents for Acids and Caustics: Not pertinent; Polymerization: Not pertinent; Inhibitor of Polymerization: Not pertinent.
- Safety ProfileSuspected carcinogen with experimental carcinogenic data. Moderately toxic by inhalation and ingestion. Mddly toxic by skin contact. An eye irritant. Mutation data reported. Can cause liver, kidney, and heart damage. Can cause dermatitis. One of the more toxic chlorinated hydrocarbons. A suggested order of increasing toxicity is dichloromethane, trichloroethylene, carbon tetrachloride, dichloropropane, dichloroethane. Animals exposed to hgh concentrations often showed marked visceral congestion, fatty degeneration of the liver, kidney, and, less frequently, of the heart. They also showed areas of coagulation and necrosis of the liver. There was found to be a heavy mortality among mice exposed to 400 ppm concentrations. A flammable liquid and very dangerous fire hazard when exposed to heat or flame. Reacts with aluminum to form aluminum chloride. This reaction, when confined, can lead to explosion. Can react vigorously with oxidizing materials. To fight fire, use water, foam, CO2, dry chemical. When heated to decomposition it emits toxic fumes of Cl-. See also CHLORINATED HYDROCARBONS , ALIPH AT1 C
- Potential ExposureDichloropropane is used as a chemical intermediate in perchloroethylene and carbon tetrachloride synthesis, and as a lead scavenger for antiknock fluids. It is also used as a solvent for fats, oils, waxes, gums and resins; and in solvent mixtures for cellulose esters and ethers. Other applications include the use of dichloropropane; as a fumigant, alone and in combination with dichloropropane, as a scouring compound; and a metal degreasing agent. It is also used as an insecticidal fumigant
- CarcinogenicityThe EPA states, “This substance
has not undergone a complete evaluation and determination
under US EPA’s IRIS program for evidence of
human carcinogenicity potential.”
An epidemiological study of 71 Italian florists, who were found to have used an average of 162 kg/year of 1,2- dichloropropane, showed that the mean frequency of peripheral lymphocyte micronuclei for the florists was higher than the mean for 75 controls, but these findings are questionable.
An oral cancer bioassay conducted in rats and mice by NTP, concluded that there was “some evidence of carcinogenicity in both male and female mice based on incidences of liver tumors (primarily adenomas, equivocal evidence of carcinogenicity in female rats based on mammary gland adenocarcinomas and no evidence of carcinogenicity in male rats.” Additional detail is provided below. Propylene dichloride was fed by gavage to rats and mice, 5 days/week for 103 weeks. Dosageswere 0 (corn oil controls), 125, and 250 mg/kg for mice and 0, 62, and 125 mg/kg for rats. Survival was reduced in high-dose female rats and mice (possibly due to infection in female mice). Body weight was reduced in high-dose rats of both sexes, and clear-cell changes and necrosis of the livers were found in high-dose female rats. The investigators concluded that dose-related increases were observed for adenomas of the liver in both male (control, 7/50; low dose, 10/50; high dose, 17/50) and female mice. The increase in the frequency of liver carcinomas supported the evidence that there was a neoplastic response in the mouse liver for both sexes (males: 11/50, 17/50, 16/50; females: 1/50, 3/50, 4/50). Hepatocytomegaly and hepatic necrosis were increased in male mice, but not in female mice.
- Environmental FateBiological. 1,2-Dichloropropane showed significant degradation with gradual adaptation
in a static-culture flask-screening test (settled domestic wastewater inoculum) conducted
at 25°C. At concentrations of 5 and 10 mg/L, percent losses after 4 weeks of
incubation were 89 and 81, respectively. The amount lost due to volatilization was only
0–3% (Tabak et al., 1981).
Soil. Boesten et al. (1992) investigated the transformation of 14C-labeled 1,2-dichloropropane under laboratory conditions of three sub-soils collected from the Netherlands (Wassenaar low-humic sand, Kibbelveen peat, Noord-Sleen humic sand podsol). The groundwater saturated soils were incubated in the dark at 9.5–10.5°C. In the Wassenaar soil, no transformation of 1,2-dichloropropane was observed after 156 days of incubation. After 608 and 712 days, however, >90% degraded to nonhalogenated volatile compounds which were detected in the headspace above the soil. These investigators postulated these compounds could be propylene and n-propane in a ratio of 8:1. Degradation of 1,2- dichloropropane in the Kibbelveen peat and Noord-Sleen humic sand podsoil was not observed possibly because the soil redox potentials in both soils (50–180 and 650–670 mV, respectively) were higher than the redox potential in the Wassenaar soil (10–20 mV).
Groundwater. According to the U.S. EPA (1986) 1,2-dichloropropane has a high potential to leach to groundwater.
Photolytic. Distilled water irradiated with UV light (λ= 290 nm) yielded the following photolysis products: 2-chloro-1-propanol, allyl chloride, allyl alcohol and acetone. The half-lives in distilled water and distilled water containing hydrogen peroxide were 50 and 30 minutes, respectively (Milano et al., 1988).
Chemical/Physical. Hydrolysis of 1,2-dichloropropane in distilled water at 25°C produced 1-chloro-2-propanol and hydrochloric acid (Milano et al., 1988). The calculated hydrolysis half-life at 25°C and pH 7 is 15.8 years (Ellington et al., 1988). Ozonolysis yielded carbon dioxide at low ozone concentrations (Medley and Stover, 1983).
Emits toxic chloride fumes when heated to decomposition (Lewis, 1990).
- Metabolic pathway1,2-Dichloropropane is quite stable to hydrolytic and microbial degradation in soils. It is metabolised rapidly and extensively in animals via a combination of gluthathione conjugation, reductive dechlorination, hydrolytic displacement of the halogen and oxidation and hydroxylation reactions (Scheme 1).
- ShippingUN1279 1,2-Dichloropropane, Hazard Class: 3; Labels: 3-Flammable liquid.
- Purification MethodsDistil the propane from CaH2. It has a limited shelf life. [Beilstein 1 IV 195.]
- Degradation1,2-Dichloropropane (1) is stable to hydrolytic degradation with a DT50
of 15.8 years (est.) at pH 7 and 25 °C (Ellington et aE., 1988). Milano et al.
(1988) reported that the dechlorination of 1,2-dichloropropane in distilled
water (25 °C) yielded 1-chloro-2-propanol(2) and HCl(3).
1,2-Dichloropropane was degraded rapidly in distilled water (DT50 50 min) after irradiation under UV light (290 nm) to yield 2, allyl chloride (4), allyl alcohol (5) and acetone (6) (Milano et al., 1988).
- IncompatibilitiesMay form explosive mixture with air. May accumulate static electrical charges, and may cause ignition of its vapors. Contact with strong oxidizers, powdered aluminum may cause fire and explosion hazard. Strong acids can cause decomposition and the formation of hydrogen chloride vapors. Reacts with strong bases; o-dichlorobenzene, 1,2-dichloroethane. Corrosive to aluminum and its alloys. Attacks some plastics, rubber, and coatings.
- Waste DisposalIncineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Consult with environmental regulatory agencies for guidance on acceptable disposal practices. Generators of waste containing this contaminant (≧100 kg/mo) must conform with EPA regulations governing storage, transportation, treatment, and waste disposal.
1,2-Dichloropropane Preparation Products And Raw materials
- 1.2-DICHLOROPROPANE (D6) 0.1G [R] 1.3-DICHLOROPROPANE SOLUTION 100UG/ML IN METHANOL 5X1ML PENTACHLOROCYCLOPROPANE Methyl 2,3-dichloropropionate 1,1,1,2,2,3,3-HEPTACHLOROPROPANE HEPTAFLUORO-2,3,3-TRICHLOROBUTANE 2,3-Dichloropropionitrile TETRACHLOROCYCLOPROPENE 1,2-DICHLOROISOBUTANE 1,1-BIS(4-CHLOROPHENYL)-1,2,2,2-TETRACHLOROETHANE Tris(2,3-dichloropropyl) phosphate 1,2-DICHLOROBUTANE 2,3-DICHLOROOCTAFLUOROBUTANE 2-CHLORO-2,2-DIPHENYLACETYL CHLORIDE 2-Chloropropionyl chloride 2,3-DICHLOROPROPIONYL CHLORIDE 2,3-DICHLOROBUTANE 2-CHLORO-2-PHENYLACETYL CHLORIDE
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